In some medical procedures, it may be necessary to retrieve a guidewire disposed within a body lumen. In particular, in some cases a guidewire may need to be advanced through a body lumen in a direction that is opposite that of the advancement of the medical device used with the guidewire. Introducing the guidewire in such a fashion is a retrograde procedure. A guidewire may be introduced in a retrograde procedure when attempting to re-vascularize a chronic total occlusion (CTO) of an arterial vessel. In such a procedure, it may be difficult to penetrate a proximal cap of the CTO with the guidewire. Accordingly, a tip portion of the guidewire is introduced at distal location relative to the CTO so that the tip portion of the guidewire can penetrate a softer distal cap of the CTO. After passing through the CTO from a distal location, the leading or distal end of the guidewire must be retrieved and passed outside the body so that the desired medical device can be received on the guidewire and delivered to the treatment site.